Time for a Closet Cleanse: These 5 Pieces Have Officially Overstayed Their Welcome

Okay, so I'm halfway through cleaning out my closet, and honestly I'm in such a mess that it feels like it would just be easier to move apartments at this point?! Now that the sugar high of getting rid of easy-to-lose items has worn off, my plan is to sit here on my bed, surrounded by piles of things I've started down the dangerous path of trying on, and procrastinate by writing my little story about the fashion items I'm finally taking out of circulation.

Let the record show that this isn't all about fashion items I regret buying or that no longer feel in style! Yes, some things I'll be donating or storing away because my style has evolved (for the moment, at least)—but this is also about the items in my wardrobe that are such winners and I wear so much they're completely thrashed beyond any hope of repair. From worn-to-death sneakers to a not-quite-me leather jacket, here's how I'll be replacing them for the season ahead.

Retiring: Some Way-Too-Dramatic Puddle Jeans

I've come to the realization that if something in my wardrobe doesn't work with flat shoes and ultra-low heels, it's barely going to be worn. So when it comes to jeans, last year's super-long styles didn't quite work out IRL. I need denim that's not going to drag along the streets in New York, so I'm back to shopping for not-too-long, relaxed, and straight-leg jeans this season.

Retiring: An Unworn Leather Moto Jacket

I have this leather jacket that's done nothing but hang in my hall closet for years. I should have given it away to a good home ages ago, but it was gifted, and I really have to fight the guilt that comes with not keeping things even when they aren't quite right for me. It deserves better than to go unworn for another season, and once I'm unburdened by its presence I can finally let myself snap up a fresh pick for winter. I'm leaning either a vintage-inspired aviator style, or something cropped and collared.

Retiring: My Beat-Up Adidas Sambas

My Sambas are in a sorry state. Not just the OG white-and-navy pair I bought first, but even my all-cream ones are looking a bit scuffed (and they're meant to be my good pair). I'm still a fan of low, retro styles, so I'll be re-upping on something similar—at the moment, I'm thinking I'll add a black style to the mix.

Retiring: A Comically Oversize Black Blazer

I love a relaxed blazer, but there's one in my closet that got a little too carried away with the whole oversized silhouette. I've been more about a cropped, collarless style of late (mine is from New Zealand brand Harris Tapper), but I also have an eye on some more cinched silhouettes that nip in at the waist.

Retiring: Some Much-Loved Cashmere Knits

I have to tell you I really get my money's worth out of my cashmere knits. There are a couple that I have to admit have finally given up the ghost. They've been razored to remove pilling so many times that they're almost see-through in some places. My favorite black crewneck is a mess but will make a good under-layer when it's freezing out, so that is going to get packed away with my thermal underwear. In the meantime, I'm looking for a couple of sweaters and cardigans to fill the gap.